The Sonogashira coupling reaction of polymer-supported propargylamine (¼ prop-2-yn-1-amine) with aryl iodides in the presence of the [Pd(PPh 3 ) 2 ]Cl 2 /CuI catalyst system produces 3-arylprop-1-yn-1-amines smoothly at room temperature (Scheme). When propargylamine is attached on Wang resin through a carbamate linker, the common problems with amino functionality in palladium-catalyzed couplings are overcome. The arylpropynamines are cleaved from the polymer with CF 3 COOH and converted into chromatographically easily separable acetamides. Our solid-phase method opens a new pathway toward precursors of pharmacologically interesting arylpropynamines and arylpropanamines.Introduction. -Aryl-and heteroarylpropanes are common precursors of biologically important natural products, e.g., of lignin [1] and lignans [2]. In addition, some 3-aryl-or 3-heteroarylpropan-1-amine derivatives have been associated with central nervous system stimulating [3], antimalarial [4], positive inotropic [5], and antifungal [6] properties. We embarked on the solid-phase Sonogashira coupling reactions of polymer-bound propargylamine (¼ prop-2-yn-1-amine) with various aryl iodides. The 3-arylpropargylamines obtained in this coupling reaction can be reduced into 3-arylpropan-1-amines of interest. On the other hand, substituted arylpropargylamines themselves are interesting compounds since some of them, or their metabolites, possess selective inhibitory activity toward physiologically significant enzymes, such as aldehyde dehydrogenase [7] and monoamine oxidase B [8].The Sonogashira coupling is an efficient palladium-catalyzed method for constructing aryl-and heteroarylacetylenes [9]. This reaction has been widely studied in liquid-phase synthesis, and due to its general efficiency, e.g., high yields, tolerance of a wide range of functional groups, and a simple one-step procedure, it has in most applications replaced the analogous reaction of copper acetylide, the Castro -Stephens reaction [10]. Although the Sonogashira coupling in solid-phase reactions has been studied to a lesser extent, there are substantial amount of reports, where the benefits of the use of polymer-supported reagents have been combined with the high performance of this reaction [11 -24]. On the other hand, both the aryl iodide and the acetylene components have been successfully used as polymer-bound reactants. For example, Moore and co-workers generated a resin-bound terminal acetylene by deprotecting the trimethylsilyl group with Bu 4 NF, and subjected it to Sonogashira conditions with (trimethylsilyl)acetylene-funtionalized aryl iodides [11]. After repeating the reaction cycles, oligomeric arylacetylenes were obtained as final products. Huang and Tour applied a related sequence-specific methodology in solid-phase synthesis of linear,
